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Your Guide to the Tennessee Songwriters Week Showcase

The Tennessee Songwriters Week Showcase is a harmony of the top 140 songwriters who advanced past their Qualifying Rounds. Sumner County is one of seven locations in Tennessee chosen to host a Songwriters Showcase where twenty of the best songwriters in Tennessee will compete at the Temple Theater in Portland, TN, to try and advance to the Tennessee Songwriters Week Finals at the Bluebird Cafe In Nashville. This music-filled weekend can be overwhelming with all the fun activities that can be found in Sumner County. Let us tune the guitar and get your weekend plans aligned with the melody of the Tennessee Songwriters Showcase with our guide to the Tennessee Songwriters Week Showcase.  


Milo Cafe may be a newer face in Portland, TN but the locals have made it a foodie haven that is raved about and visited frequently by visitors and loyal customers alike. This is the perfect first stop for lunch to recharge and reenergize before taking on Portland’s Main Street. 

A burger from Milo's Cafe the perfect lunch spot for the Tennessee Songwriters Week Showcase

SHopping on Main Street

After a full meal at Milo’s, it is time to take to the streets of Portland’s Main Street and indulge in a shopper’s haven. From southern belle classics to casual clothing, you will find your next southern charm while hitting the streets and shopping on Portland’s Main Street. 

Don’t drop your bags off just yet! Take your travels to Sumner Crest Winery on the edge of Portland and sip a loved Southern creation. Offering different tiers of tastings, there is a tasting that suits everyone’s wine level. From small flights to guided wine tastings, you’ll need your shopping bags to carry your favorite bottle of wine… or two. 

Outside Patio of Sumner Crest Winery. A stop on the Tennessee Songwriters Week Showcase guide.

Dinner Senior Fajitas

Don’t skip out on dinner or you will miss a delicious collaboration of spices and Hispanic dishes that take your palate on a journey to flavortown. Senior Fajitas has been a staple in Portland that has left guests wanting more and more. A dinner of this caliber is a flavor sensation you don’t want to miss out on. 

Tortas at Senior Fajitas in Portland, Tennessee the dinner spot for the Tennessee Songwriters Week Showcase Guide.

After a delicious dinner it is time to head back to Portland’s Main Street where the perfect view of the Temple Theater will lead you to the Tennessee Songwriters Week Showcase. Take in the Tennessee talent of songwriters competing for a chance to take the stage in the Tennessee Songwriters Week Finals at the legendary Blue Bird Cafe in Nasvhille. 

Artist playing on stage at the Tennessee Songwriters Week Shocase

Relax at Hotel

After a fun day exploring the southern treasure of Portland and all it has to offer, then singing along to the talented songwriters at the Tennessee Songwriters Week Showcase, it’s time to head back to the hotel and rest up for another big day in Sumner County. 

hotel bed


Continue in the music theme of the weekend at Music City Diner. You’ll need lots of time to look over their menu of delicious homemade breakfast plates, like their stomach-filling french toast or fluffy pancakes. Save room for dessert because once you pass their dessert counter, you’re going to want to buy the whole case! 

Breakfast of pancakes at Music City Diner

That delicious meal won’t weigh you down once you see the beauty of historic Downtown Gallatin. Home to numerous boutiques and unique shops that always leave you with a friendly “come back, ya’ll”. 

You’ll work up an appetite by finding your new trend-setting clothes, and Lime Deli has your light lunch needs covered. From light, freshly made sandwiches to lush green salads, Lime Deli will give you the delicious energy kick needed to take on the rest of Sumner County.

Small Salad from Lime Deli

Get connected with your roots as you take a hike through the gorgeous Bledsoe Creek State Park. With multiple trails for all experience levels and a mile of ADA-compliant trails, this destination is a perfect breath of fresh air. 

People hiking at Bledsoe Creek State Park

Take a load off and relax while creating a keepsake of your Sumner County trip at Board and Brush! With workshops of your choosing, Board and Brush allows you to sip and create a wood piece that is sure to hold and remind you of the memories you made in Sumner County. 

Class at Board and Brush

This local treasure creates authentic Italian dishes that amaze guests and the story of their creation leaves guests making reservations for their next trip to Sumner County. Trattoria La Caverna is the perfect dinner location to end your Saturday before taking on Sumner County’s nightlife. 

Look no further for your perfect night lift destination than Edit. Owned by passionate Nashville foodies and mixologists, Edit brings a spice to Sumner County’s nightlife. Their famous drink, “The Fox Hollow,” has been featured on the Kelly Clarkson show and leaves a lasting taste that is smooth to every guest. 


Pack at Hotel

It’s time to pack up all your Sumner County souvenirs and get the car loaded to trek back home. Make sure you get it all packed away.   

This is a meal you will want to keep ordering more and more from so you don’t have to leave. From the waterfront views to the sensational dishes, the Rudder is the perfect cherry on top of your culinary journey in Sumner County. 

Your music weekend would not be complete without stopping by some of the legendary Tennessee Music Pathway Markers! These markers signify legendary figures in Tennessee’s music heritage that called Sumner County home. You can find Johnny Cash and Taylor Swift’s music pathway markers on the way to your final stop before heading home. 

Taylor Swifts Music Pathway Marker in Hendersonville, Tennessee

The last stop on your way home from Sumner County and your music filled weekend is at Half Batch Brewing! Half Batch recently opened up their new brewery that is a local favorite. Stop in and have a pint of The Fulkin. A Scottish Ale that won a gold medal at the World Beer Cup in 2023. The equivalent of winning an Olympic Gold Medal! 

Pint of the Fulkin at Half Batch

The Tennessee Songwriters Week Showcase is a yearly anticipated event across Tennessee. The celebration of the craft that put Tennessee on the map is an opportunity to catch some of the music industry’s brightest up-and-coming artists at historical venues across Tennessee. Make the most out of your music-filled weekend in Sumner County with our Tennessee Songwriters Week Guide and visit our events page for more events coming to Sumner County in 2024! 

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